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Chirality

Chirality

Chirality is a term that describes the lack of mirror symmetry in an object. In other words, chiral objects cannot be superposed on their mirror images. For example, our feet are chiral, as the mirror image of the left foot, the right foot, cannot be superposed on the left foot.
Chiral objects exhibit a sense of handedness when they interact with another chiral object. For example, our left foot can only fit in the left shoe and not in the right shoe. Achiral objects — objects that have...

Chirality in Nature

Chirality in Nature

Chirality is the most intriguing yet essential facet of nature, governing life’s biochemical processes and precision. It can be observed from a snail shell pattern in a macroscopic world to an amino acid, the minutest building block of life. Most of the snails around the world have right-coiled shells because of the intrinsic chirality in their genes. All the amino acids present in the human body exist in an enantiomerically pure state, except for glycine - the sole achiral amino acid.

Chirality at Nitrogen, Phosphorus, and Sulfur

Chirality at Nitrogen, Phosphorus, and Sulfur

Chirality is most prevalent in carbon-based tetrahedral compounds, but this important facet of molecular symmetry extends to sp3-hybridized nitrogen, phosphorus and sulfur centers, including trivalent molecules with lone pairs. Here, the lone pair behaves as a functional group in addition to the other three substituents to form an analogous tetrahedral center that can be chiral.
A consequence of chirality is the need for enantiomeric resolution. While this is theoretically possible for all...

Molecules with Multiple Chiral Centers

Molecules with Multiple Chiral Centers

Molecules that possess multiple chiral centers can afford a large number of stereoisomers. For instance, while some molecules like 2-butanol have one chiral center, defined as a tetrahedral carbon atom with four different substituents attached, several molecules like butane-2,3-diol have multiple chiral centers. A simple formula to predict the number of stereoisomers possible for a molecule with n chiral centers is 2n. However, there can be a lower number where some of the stereoisomers are...

EDTA: Auxiliary Complexing Reagents

EDTA: Auxiliary Complexing Reagents

EDTA titrations are usually carried out in highly basic conditions, where the fully deprotonated form of EDTA, Y4−, actively complexes with the free metal ions in the solution. Several metal ions precipitate as hydrous oxide (hydroxides, oxides, or oxyhydroxides) under these conditions, lowering the concentration of free metal ions in the solution. For this reason, auxiliary complexing agents or ligands such as ammonia, tartrate, citrate, or triethanolamine are used in EDTA titrations to...

Dehydration Synthesis

Dehydration Synthesis

Overview
Dehydration synthesis (also called a condensation reaction) is the chemical process in which two molecules covalently link together to form a new molecule, along with the release of a water molecule. Many physiologically important compounds form by dehydration synthesis reactions, such as complex carbohydrates, proteins, DNA, and RNA.
Synthesis of carbohydrates
Sugar molecules are covalently linked together by dehydration synthesis. During the reaction, the hydroxyl (-OH) group from...

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Related Experiment Video

Updated: Feb 7, 2026

Enzymatic Cascade Reactions for the Synthesis of Chiral Amino Alcohols from L-lysine

Enzymatic Cascade Reactions for the Synthesis of Chiral Amino Alcohols from L-lysine

Published on: February 16, 2018

Unlocking P(V): Reagents for chiral phosphorothioate synthesis.

Kyle W Knouse¹, Justine N deGruyter¹, Michael A Schmidt²

¹Department of Chemistry, The Scripps Research Institute, 10550 North Torrey Pines Road, La Jolla, CA 92037, USA.

Science (New York, N.Y.)

|August 4, 2018

Summary

Researchers developed a new phosphorus(V)-based method for synthesizing phosphorothioate nucleotides, crucial for antisense oligonucleotide therapeutics and cyclic dinucleotide synthesis. This approach offers a stereocontrolled, efficient, and simpler alternative to existing phosphorus(III) methods.

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A Novel Saturation Mutagenesis Approach: Single Step Characterization of Regulatory Protein Binding Sites in RNA Using Phosphorothioates

A Novel Saturation Mutagenesis Approach: Single Step Characterization of Regulatory Protein Binding Sites in RNA Using Phosphorothioates

Published on: August 21, 2018

Area of Science:

Medicinal Chemistry
Organic Synthesis
Nucleic Acid Chemistry

Background:

Phosphorothioate nucleotides are vital analogs of native phosphodiesters with applications in antisense oligonucleotide (ASO) therapeutics and cyclic dinucleotide (CDN) synthesis.
Current methods for stereocontrolled synthesis of phosphorothioates rely on phosphorus(III) reagents, limiting efficiency and control.

Purpose of the Study:

To introduce a novel phosphorus(V)-based reagent platform for the stereocontrolled synthesis of phosphorothioate nucleotides.
To demonstrate a programmable, traceless, and diastereoselective method for phosphorus-sulfur incorporation.

Main Methods:

Development of a new phosphorus(V)-based reagent system for nucleoside modification.
Application of the reagent system to the synthesis of various nucleotidic architectures, including ASOs and CDNs.
Stereochemical analysis and validation of the synthesized compounds.

Main Results:

Successful demonstration of a P(V)-based platform for programmable, traceless, and diastereoselective phosphorus-sulfur incorporation.
Robust and stereocontrolled synthesis of diverse nucleotidic structures, including ASOs and CDNs.
The developed protocol is efficient, inexpensive, and operationally simple.

Conclusions:

The novel P(V)-based reagent platform provides a significant advancement in the stereocontrolled synthesis of phosphorothioate nucleotides.
This method overcomes limitations of P(III)-based approaches, offering a more accessible route for therapeutic oligonucleotide and CDN development.
The protocol's efficiency and simplicity facilitate broader applications in pharmaceutical research and development.